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Enantioselective Organocatalytic α‐Alkylation of Ketones by S N 1‐Type Reaction of Alcohols
Author(s) -
Trifonidou Maria,
Kokotos Christoforos G.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101509
Subject(s) - enantioselective synthesis , chemistry , alkylation , pyrrolidine , catalysis , organocatalysis , carbocation , organic chemistry , ring (chemistry) , medicinal chemistry
The enantioselective α‐alkylation reaction of cyclic ketones is described. Our catalyst, based on a “privileged” pyrrolidine ring bearing a chiral thioxotetrahydropyrimidinone ring, is a highly reactive catalyst for cyclic ketones. When this catalyst was coupled with in situ generated carbocations derived from alcohols, the corresponding α‐alkylated adducts were obtained in moderate to quantitative yields and low to high enantioselectivities (up to 80 % ee ). The catalyst loading can be efficiently reduced to 10 %, which is the lowest value reported in the literature for such an organocatalytic transformation.